Director of Engineering, Freedom

Information Technology Toronto, Canada


Director of Engineering, Freedom

The Director of Engineering for Freedom will lead and oversee all technical aspects of the development of the Freedom API Platform. Reporting to the VP of Engineering for Checkout 51, and managing a team of developers and testers, you will own all technical facets of this product, including development, testing, and certain aspects of operations as well.

In addition to the technical responsibilities of this role, you will draw upon your experience as a people manager to help ensure the consistent delivery of software while maintaining a healthy and positive work environment. We will be counting on you lead the enhancement and evolution of the Freedom API, while also ensuring the career growth of the engineers under your supervision. This role involves close collaboration with our DevOps, Product, and Business Development teams.


Product & Technology
  • Maintain and manage the technology roadmap for your team(s).
  • Provide architectural guidance to your team, ensuring that they align with the needs of the product and our overall technology strategy
  • Participate in the resolution of production incidents in either a hands on or oversight capacity.
  • Provide recommendations to the Product team in Build vs. Buy scenarios.
  • Ensure the correct prioritization of maintenance activities, including operational maintenance, technical debt remediation and security enhancements
  • Collaborate with your peers in the engineering organization to standardize technology choices across development teams
  • Assist Business Development team by acting as a technical consultant to potential partners.
  • Manage the growth of your team, on-boarding new hires and overseeing recruitment for your team
  • Establish professional development plans for your direct reports
  • Conduct annual performance reviews and quarterly goal setting for your team
  • Create and maintain resourcing plans to deliver on the product roadmap
  • Manage temporary staff (Agencies / Contractors) as and when the need arises.
  • Maintain a positive and collaborative work environment by upholding Checkout51's cultural values
  • Collaborate with scrum masters to ensure consistent performance of the development teams in your organization
  • Collaborate with other functional groups (Product, DevOps, Client Success, Sales Strategy) to ensure that we are consistently delivering a high quality product.
Technical Skills
  • Strong working knowledge of PHP, JavaScript and a statically typed programming language (e.g. Java, C#, Go, TypeScript etc.)
  • Strong understanding of object oriented and functional programming paradigms
  • Strong understanding of software testing methodologies including Unit, Integration, Functional, and Performance and Load Testing
  • Strong understanding of web service design using both REST and RPC paradigms
  • Strong understanding of SOA and Microservices architectures,
  • Deep knowledge of AWS Compute, Storage and Database services including EC2, ECS, RDS, S3, Lambda, Athena, Glue, Kinesis
  • Working knowledge of React.js and GraphQL
  • General knowledge of secure development practices